2-Methylbutanal → 5-Chloro-2-(2-methyl-butylamino)-benzoic acid

HRID 1784249Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][CH:13]([CH2:16][CH3:17])[CH:14]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][CH2:12][CH:13]([CH3:14])[CH2:16][CH3:17])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

Reactant 3

HCID 72842-Methylbutanal

HCID 124762-Amino-5-chlorobenzoic acid

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 635380315-Chloro-2-(2-methyl-butylamino)-benzoic acid

Procedure

5-chloro-2-(2-methyl-butylamino)-benzoic acid was prepared from 2-amino-5-chloro-benzoic acid (23.31 mmol, 4.0 g) and 2-methylbutyraldehyde (23.31 mmol, 2.0 g) with sodium triacetoxyborohydride (96.62 mmol, 9.88 g) as per Procedure G (5.0 g).

Sources & evidence

ORD record: ord-3caad9211a7240708ab6639c302eda31
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501538B2

Reaction notes

Loading…